
1611 CHESTNUT AVENUE, WINTER PARK, FL, 32789
Active3 days on marketListed Oct 13, 2026MLS #O6449003
About this home
1611 CHESTNUT AVENUE
Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering nearly 3,000 square feet of thoughtfully designed living space in the highly desirable 32789 ZIP code. Far beyond cosmetic updates, this home has undergone a substantial transformation, including major additions to the rear and second floor, creating a spacious, versatile layout with high-quality finishes and modern comforts throughout. The result is a home that combines the established character of its surroundings with the space and functionality of a contemporary residence. The beautifully redesigned kitchen features quartz countertops, stainless steel appliances, a generous island, farmhouse sink, and adjoining pantry, opening to inviting living and dining areas. Whether preparing a quiet dinner or hosting a gathering, the kitchen's generous workspace and connection to the surrounding rooms make it a natural center of daily life. A separate, expansive family room showcases a stone wood-burning fireplace and custom built-ins, providing another comfortable setting for relaxing or entertaining. Engineered hardwood and luxury vinyl flooring, designer tilework, upgraded fixtures, and beautifully appointed bathrooms reflect the attention and investment devoted to this home. The thoughtful separation of living spaces gives everyone room to enjoy the home in their own way without sacrificing the ease of gathering together. The impressive upstairs primary retreat provides exceptional privacy, featuring a spacious en-suite bathroom with freestanding soaking tub, double vanity, walk-in closet, and dedicated built-in office alcove. Occupying its own upper-level space, this generously proportioned suite feels like a retreat within the home, with room for both a restful bedroom setting and a practical workspace. Three additional bedrooms are located downstairs, including two with en-suite bathrooms. One enjoys an adjoining sitting room with sliding doors opening to the backyard, creating an ideal arrangement for extended family, guests, or multigenerational living. This flexible layout is equally appealing for those seeking a private guest area, a home office, or separate spaces for different daily routines. Additional improvements include an updated roof, newer AC system, a dedicated laundry room, attached two-car garage, and a private fenced backyard surrounded by mature landscaping. The outdoor setting provides space to unwind, enjoy fresh air, or create a welcoming area for casual get-togethers, while the mature trees and greenery reinforce the charm of this established neighborhood. Situated in Winter Park's established Lake Knowles Terrace neighborhood, the property is surrounded by charming residences, beautifully renovated homes, and impressive newer custom construction. Here, brick-paved streets and a canopy of mature oaks create a distinctive streetscape that is increasingly difficult to find. Enjoy convenient access to the Winter Park Chain of Lakes, Winter Park Golf Course, Phelps Park, the YMCA, and the renowned shopping, dining, and cultural attractions of Park Avenue. From neighborhood walks beneath the oaks to an afternoon along Park Avenue, this address places many of Winter Park's most loved destinations close to home. An exceptional combination of extensive improvements, generous living space, flexible accommodations, and a highly sought-after Winter Park location.
Facts & features
The home at a glance
4
Bedrooms
4
Bathrooms
2,916
Sqft
0.17 ac
Lot size
1973
Year built
Two
Levels
$338
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$6,152 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$6,152/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−45.8%
$/sqft vs Winter Park actives
$338 vs $330
Days on market
3 vs 56 typical
Where $338/sqft sits among the 333 Winter Park actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Lake Knowles Terrace
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Lake Knowles Terrace — neighborhood snapshot
Population
1,017
Median age
49
Median income
$193,750
Median home value
$808,200
Avg household
3
Households w/ children
126
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$470K → $530K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
158 of 333
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 23% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 1611 CHESTNUT AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$1,690,000
1630 CHESTNUT AVENUE · same community
3 bd · 4.5 ba · 3,164 sqft · $534/sqft · 70 DOM
Sold · Feb ’26$1,150,000
1611 WALNUT AVENUE · same community
4 bd · 3 ba · 2,635 sqft · $436/sqft · 8 DOM
Sold · Jul ’26$1,450,000
1660 WALNUT AVENUE · same community
4 bd · 3.5 ba · 2,249 sqft · $645/sqft · 43 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Kevin Johnson
CEO & Managing Broker · CENTURY 21 Edge
Tours, negotiation, and every question about 1611 CHESTNUT AVENUE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1611 CHESTNUT AVENUE — before you fall in love.
See it in person
Schedule a tour
Live availability from Kevin's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1611 CHESTNUT AVENUE FAQs
What would the monthly payment be for 1611 CHESTNUT AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,152/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 1611 CHESTNUT AVENUE?+
The most recent tax bill on record (2026) was $3,697. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Park?+
At $985,000, this home is listed about 71% above the Winter Park median of $575,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1611 CHESTNUT AVENUE?+
Lakemont Elementary (elementary), Maitland Middle (middle), Winter Park High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$985,000 runs 23% above the WINTER PARK 32789 median — but at 2,916 sqft it's also 62% larger than the typical Winter Park listing.
02Fresh on the market
Only 3 days on market in a Winter Park market that averages 56 — if it fits, move quickly.
03Strong assigned schools
Lakemont Elementary, Maitland Middle, Winter Park High — Winter Park High rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of OLYMPUS EXECUTIVE REALTY INC · Gunel Aydamirli. MLS #O6449003.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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